Trifluoromethylation of aromatic alkenes by visible-light-driven photoredox catalysis: Direct conversion of alkenes to 3-trifluoromethyl-1-propenyl and 1,3-bis(trifluoromethyl)-1-propenyl derivatives

Abstract

Photoredox-catalyzed trifluoromethylation of alkenes using Umemoto's reagent as a CF3 source under visible light irradiation has been developed. A Ru photocatalyst, [Ru(bpy)3](PF6)2 (bpy = 2,2′-bipyridine), is useful for the present trifluoromethylation and preferable formation of 3-trifluoromethyl-1-propenyl derivatives is observed. Use of an excess amount of Umemoto's reagent readily induces double trifluoromethylation of electron-rich alkenes, resulting in 1,3-bis(trifluoromethyl)-1-propenyl skeleton.